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Synthesis and anti-Trypanosoma cruzi activity of derivatives from nor-lapachones and lapachones

2008; Elsevier BV; Volume: 16; Issue: 9 Linguagem: Inglês

10.1016/j.bmc.2008.03.032

1464-3391

Eufrânio N. da Silva Júnior, Maria Cecília B. V. de Souza, Michelle C. Fernandes, Rubem F. S. Menna‐Barreto, Maria do Carmo F. R. Pinto, Francisco de Assis da Silva Lopes, Carlos A. de Simone, Carlos Kleber Z. Andrade, António Pinto, Vı́tor F. Ferreira, Solange L. de Castro,

Synthesis and Reactions of Organic Compounds

New naphthoquinone derivatives were synthesized and assayed against bloodstream trypomastigote forms of Trypanosoma cruzi, the etiological agent of Chagas' disease. The compounds were rationalized based on hybrid drugs and appear as important compounds against this parasite. From nor-lapachol were prepared five substituted ortho-naphthofuranquinones, a non-substituted para-naphthofuranquinone, a new oxyrane and an azide and from α-lapachone a new non-substituted para-naphthofuranquinone. Other five substituted ortho-naphthofuranquinones recently designed as cytotoxic, were also evaluated. The most active compounds were the ortho naphthofuranquinones 3-(4-methoxyphenylamino)-2,3-dihydro-2,2-dimethylnaphtho[1,2-b]furan-4,5-dione and 3-(3-nitrophenylamino)-2,3-dihydro-2,2-dimethylnaphtho[1,2-b]furan-4,5-dione with trypanocidal activity higher than that of benznidazole, the standard drug. The compounds were rationalized based on hybrid drugs and appear as important compounds against T. cruzi. The trypanocidal activity of these substances endowed with redox properties representing a good starting point for a medicinal chemistry program aiming the chemotherapy of Chagas' disease.